Synthesis of 5?Azatetracene and Comparison of Its Optical and Electrochemical Properties with Tetracene

A four-step route for the synthesis of 5-azatetracene (benzo[b]acridine) has been developed, employing a base-catalysed Friedlander condensation reaction between 3-amino-2-napthaldehyde and cyclohexanone as key step followed by dehydrogenation intermediate. The optical electrochemical properties were investigated UV-vis photoluminescence spectroscopy, cyclic voltammetry compared with those tetracene. It is found that shows broader absorption in visible region than tetracene, exhibits higher luminescence quantum efficiency, possesses lower-lying LUMO level smaller HOMO-LUMO band gap. Time-resolved PL spectroscopy was used to elucidate reasons more efficient 5-azatetracene. Field-effect transistor measurements revealed ambipolar nature charge transport